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For sale
  • Price cut: $174K (5/23)
    $1,725,000

    22542 Jolly Roger Dr, Cudjoe Key, FL 33042

    4beds
    2,440sqft
    : 
    $10,078/mo
    Get pre-qualified
    Single Family Residence
    Built in 1982
    6,534 Square Feet Lot
    $1,650,600 Zestimate®
    $707/sqft
    $-- HOA

    What's special

    Open-concept layoutFrame ocean viewsRich wood beamsRenovated and modern kitchenPrivate boat launchDining spaceGenerous outdoor spaces
    Stunning oceanfront home. This 4-bedroom, 3-bathroom home is a testament to coastal architecture. Broad, covered balconies, generous outdoor spaces, and a private boat launch capitalize on Keys waterfront living. Large impact glass doors and windows frame ocean views and invite natural light into every room. Soaring, 26' ceilings enhance the open-concept layout with rich wood beams amplifying the aesthetic. The main floor living space includes a renovated and modern kitchen, dining space, living room, laundry, two bedrooms and two bathrooms. Ascend to the upper floor to find a third bedroom perched at the top of the stairs. A catwalk connects the fourth bedroom with ensuite bath and walkout deck that provides spectacular panoramic open water views. The home itself tells a story through design. Restored to its former glory, with additional modern amenities, and blending rustic accents with open, light-filled spaces to showcase the oceanfront setting. This home needs to be seen to be fully appreciated. Schedule your showing today!
    97 days
    |
    991
    |
    51
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Lauren Hoefert Dunn 305-394-3717,

    Coldwell Banker Schmitt Islamorada,

    Sarah Eckert 772-501-6576,

    Coldwell Banker Schmitt Real Estate Co. (KW)

    Source: FLKMLS,MLS#: 619558MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 3
      • Full bathrooms: 3
      Cooling
      • Central Air
      Appliances
      • Included: Washer, Dryer, Dishwasher, Refrigerator, Oven, Wine Cooler, Stainless Steel Appliance(s)
      Features
      • Built-in Features, Granite Counters, Walk-in Closet(s), Quartz Countertops
      Interior area
      • Total structure area: 2,440
      • Total interior livable area: 2,440 sqft

      Property

      Parking
      • Parking features: Open
      • Has uncovered spaces: Yes
      Features
      • Patio & porch: Open Porch/Balcony, Deck
      • On waterfront: Yes
      Lot
      • Size: 6,534 Square Feet
      Details
      • Parcel number: 00180480000000
      • Zoning: IS - Improved Subivision District

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence
      Materials
      • Frame
      Condition
      • Updated/Remodeled
      • New construction: No
      • Year built: 1982

      Community & HOA

      Community
      • Subdivision: Cutthroat Harbor Est (23.0)
      HOA
      • Has HOA: No
      • Services included: None
      Location
      • Region: Cudjoe Key

      Financial & listing details

      • Price per square foot: $707/sqft
      • Tax assessed value: $1,403,446
      • Annual tax amount: $12,645
      • Date on market: 4/18/2026

        Estimated market value

        $1,650,600

        $1.57M - $1.73M

        $6,378/mo

        Price history

        DateEventPrice
        5/23/2026Price change$1,725,000-9.2%$707/sqft
        Source: FLKMLS #619558 Report a problem
        4/18/2026Price change$1,899,000-9.6%$778/sqft
        Source: FLKMLS #619558 Report a problem
        2/26/2026Listed for sale$2,100,000-4.5%$861/sqft
        Source: FLKMLS #618818 Report a problem
        2/20/2026Listing removed$2,200,000$902/sqft
        Source: Key West AOR #618018 Report a problem
        2/14/2026Price change$2,200,000-4.3%$902/sqft
        Source: Key West AOR #618018 Report a problem
        1/9/2026Listed for sale$2,299,000+15.1%$942/sqft
        Source: Key West AOR #618018 Report a problem
        1/9/2026Listing removed$1,998,000$819/sqft
        Source: FLKMLS #616688 Report a problem
        10/2/2025Listed for sale$1,998,000-0.1%$819/sqft
        Source: FLKMLS #616688 Report a problem
        6/26/2025Listing removed$1,999,800$820/sqft
        Source: FLKMLS #615091 Report a problem
        5/20/2025Listed for sale$1,999,800-10.9%$820/sqft
        Source: FLKMLS #615091 Report a problem
        5/20/2025Listing removed$2,245,000$920/sqft
        Source: FLKMLS #612454 Report a problem
        5/5/2025Price change$2,245,000-2.2%$920/sqft
        Source: Key West AOR #612454 Report a problem
        4/11/2025Price change$2,295,000-4.2%$941/sqft
        Source: FLKMLS #612454 Report a problem
        1/28/2025Price change$2,395,000-4%$982/sqft
        Source: FLKMLS #612454 Report a problem
        11/28/2024Listed for sale$2,495,000+9.7%$1,023/sqft
        Source: Key West AOR #612454 Report a problem
        8/30/2024Listing removed$2,275,000+5.8%$932/sqft
        Source: Key West AOR #610727 Report a problem
        7/11/2024Listed for sale$2,150,000+72%$881/sqft
        Source: FLKMLS #610727 Report a problem
        7/28/2023Sold$1,250,000-10.7%$512/sqft
        Source: Key West AOR #605151 Report a problem
        5/12/2023Contingent$1,400,000$574/sqft
        Source: MLKAR #605151 Report a problem
        5/8/2023Listed for sale$1,400,000$574/sqft
        Source: MLKAR #605151 Report a problem
        5/3/2023Contingent$1,400,000$574/sqft
        Source: MLKAR #605151 Report a problem
        5/3/2023Listed for sale$1,400,000$574/sqft
        Source: Key West AOR #605151 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$12,646 -3.1%$1,403,446 -3%
        2024$13,049 +66.8%$1,447,446 +87.4%
        2023$7,822 +12.2%$772,244 +7%
        2022$6,968 +7.2%$721,598 +6.9%
        2021$6,498 +6.8%$674,986 +3.7%
        2020$6,087 $651,005 +20%
        2019$6,087 +21.4%$542,635 +4.9%
        2018$5,014 -4.3%$517,441 -12.7%
        2017$5,240 -6.2%$592,695 +7.7%
        2016$5,586 +3.7%$550,241 +1.3%
        2015$5,387 $542,959
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

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        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
        Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
        See how much you could borrow to make a competitive offer.

        Climate risks

        Neighborhood: 33042

        Getting around

        8 / 100
        Car-Dependent
        46 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating

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